The Trouble with Tess 1
Introduction:
Mooching sister
After my parents divorce I lived in Chicago with my dad, I finished College and managed to go right into hospital administration. I was able to start with a junior position right out in Chicago which was nice but I finally managed to land a better job, at the hospital that my mom works at. I had been living on my own for almost 3 years in Chicago but in coming back home it made it lots easier to just move back in with mom.
Moving back home is always hard although it was also a chance to help mom with my sister Tess. Tess dropped out of college and at 19 had a good start on becoming our families first alcoholic. She refused to get a job, even try to get a job, and was apparently also ruining any chance for a social life for my mom. My mom really shouldn’t have any problem with dating, that’s for sure. She has huge pendulous breasts and a really pretty face. Nice figure overall too.
Apparently my sister Tess works very hard at driving men away so that she can continue to “keep things the way they are” well that was obviously going to change with me moving into their 2 bedroom apartment. The plan that mom and I had, was for me to stay there rent free, save money and then buy a house. That if Tess didn’t turn herself around then mom would put Tesses name on the lease and just move out, and in with me where I would reciprocate the rent free arrangement till mom was on her feet again. Tess of course, was not aware of these plans. We figured that it would take a year or two for me to save a good down payment anyway.
Well the move in went pretty much as well as we expected. My sister threw a fit, refused to help and began threatening to move out. When she realized that the threat to move meant nothing, she dropped it and just focused on making life hell.
Well the first problem was living arrangements. 3 adults and 2 bedrooms. That was solved the first night, mom works nights on the floor and I was day shift in administration. So our solution was that mom and I separately shared the same bed. This also made my sister furious, she immediately began calling me a pervert and asking me if I liked sucking on my mommas titties.
This in turn infuriated my mom as well, as a result mom began throwing it right back in my sisters face saying that she looked forward to me suckling her breasts as Tess had ruined any other chances she had at finding a man to play with.
This caused such a reaction in my sister that mom actually called me on her way home from work to ask me if I would go along with the charade. Tess was losing her mind over the idea that we were fooling around, it might break something loose and cause my sister to grow up, move out, get a job, who knows, something.
The first day that we had a good fight over my staying, after establishing that plan, went about like this. Tess made some crack about me suckling on my moms tits, Mom was in the kitchen which was attached to the living room where Tess and I were at. I immediately replied to Tess “in case you haven’t noticed, mom has some absolutely beautiful breasts, I love suckling on them” Tess flipped. I walked into the kitchen and gave mom a peck on her ear while whispering “how big are your nipples?” Mom flushed a deep red and looked down, then right back up with a big smile and held out her hand indicating with her finger and thumb a round area almost the size of the palm of your hand. Moms hand was below the half wall that divided the kitchen area. Tess was speechless so mom jumped in with “your brother is very considerate, since you’ve driven all my potential boyfriends away he’s all I can find”
Tess ran to her room slamming the door, mom now looked at me with a shocked look on her face and asked why I needed to know about her nipples. I told her that I didn’t know if Tess had seen them or not and I didn’t want to describe the wrong size to her if I had to. She smiled and told me that I was wicked, but a good kind of wicked. Especially since I was so kind about her saggy old breasts. I kind of instinctively said “well they really are beautiful” and now mom was shocked into silence. That pretty much ended our first fight with Tess, she avoided both me and mom for the next two days. However whenever Tess was within earshot in her room I would pay mom compliments about how she looked. I could tell that mom loved the attention even though none of it was dirty.
That brought us to the weekend, we really hadn’t planned that far ahead so now all three of us were home together at the same time. Mom was in bed and Tess was glaring at me, I was able to take off and do some shopping and got a gym membership. That got me home closer to the time that mom was getting up. Tess started up screaming and that brought mom out of bed wearing her night gown. If it wasn’t for my screaming sister I probably would have popped wood on the spot. Moms breasts were pretty much totally visible. Mom had obviously told the truth about the size of her nipples. They were swinging and swaying back and forth with every move mom made. That and I saw a obvious dark triangle down between her legs. Mom and Tess were busy arguing and I was busy ogling. I never heard a word of their argument, it ended when Tess stormed out of the house.
Suddenly it got real quiet and I found my self slowly looking up to my moms face which up till now I had not seen. She was still flushed red from screaming at my sister and was now staring at me and almost screamed at me saying “what are you looking at” I kept my wits and said “I was right, they are beautiful” Mom switched gears, looked shocked for a second then ran off to her bedroom. She came back out a while later fully dressed and almost afraid to look at me. She was obviously avoiding eye contact when she started saying that this might be a bad idea. That with the things that I was saying about her. The compliments and attention were bringing out “frustrations” that were hard to deal with. I told her that I could stop if she wanted but that I really had been telling the truth. That if Tess does grow up, get a job or otherwise move out. That I was certain that she wouldn’t be staying single for long. Mom started crying which led to more talking. Time went by I guess and it all ended in an awesome titty hug. Mom just wrapped her arms around me and hugged without worrying about squishing her tits into me.
Timing could not have been better, Tess burst back into the apartment with a fresh load of liquor. Spotting me and mom in a hug she spat out the complaint “get a room” Mom beat me to the reply. She quietly and rather proudly said “as a matter of fact we do have a room, here in MY apartment” Mom then led me into “our” room and had me lay on the bed. No sex, but a fantastic back rub. As mom pushed in a few times with the rub I groaned. Tess, in the other room screamed. Mom got into it and started really giving me a deep massage. She managed to get my back to pop and every time that happened I gave a “AH” and with some of the deep rubs she got more of a OOOHHHH. We heard the door slam as Tess left the house. Mom however did not stop, she kept rubbing but more softly and even though it was day time for me I fell asleep. I woke up later on with mom laying partially on top of me. She was still fully dressed but she had an arm around me. I reciprocated putting an arm around her and pulling her towards me falling back asleep myself.
We woke up to the sound of the police knocking on the door. Tess called the police to say that her brother was raping her mother. I got hauled out on the front lawn and told them my sister was a drunk who was mooching off of mom. That I was there rent free so I could buy a house. That if my sister didn’t straighten up that my mom would be moving in with me while leaving my sister behind. Another cop interviewed mom inside while I was explaining this. They compared notes, both of us said the same thing. They read Tess the riot act and told her that she’d be going to jail if she called like that again.
When the cops had left mom quietly made the comment that we now knew what to say in the future if anyone ever heard of Tess’s complaints. Her comment didn’t mean much to me till the next day when we were home alone again, just the three of us. Mom wandered out of her bedroom when she woke up in the afternoon, wearing the same see through nightie. My sister blurted out a disgusted “oh my gawd” I just stared as mom wandered into the bathroom. Her breasts were obviously swaying back and forth with her huge nipples clearly on display. Just before walking into the bathroom mom did a little turn just to show us her bare ass through the thin nightie. I absolutely absorbed the view of her ass as her cheeks wiggled a little before she disappeared into the bathroom. As mom was coming back out Tess started making snide comments about moms saggy tits. I cut in saying that the sag was just fine as long as she remembered what direction they needed to sag in. That brought mom to a standstill in her walk back to her room. She asked what direction they were supposed to sag in. I said nothing I just opened my mouth and pointed at it with my finger. Mom got a slutty smile and my sister screamed.
As mom finished walking back to her room she looked at my sister and just hissed at her “call the police again and you go to jail” then motioned for me to follow her. I did exactly what I wanted to do, I followed mom. Now we were in her room, the door was shut and mom was functionally naked in front of me. She asked me if I thought she was taking this too far. I told her that she’d know when she’s taken it too far. She asked how I would tell her that she was going too far. I told her that I wouldn’t tell her anything, I’d just be bending her over and nailing her from behind. She looked shocked for a second and then just smiled. She started talking by referring to yesterdays conversation. She said she hadn’t really explained her self properly. Some of the frustrations that she was feeling now, were that she was getting turned on by this game. That my compliments towards her were having “that” kind of effect on her. Then she said that this game we were playing was unfairly affecting her. I asked what was unfair about it and she said that I had gotten to see her, but that she had never gotten to”see” me in return. Mom then looked at my pants and nodded her head down. I pulled them down showing my tented briefs. I was so hard the head was poking above my elastic waste band.
Mom smiled and said “ohh, does he like he like the game mommy is playing too?” She knelt down in front of me and pulled my shorts down. She started lifting up on my shirt so I took it off. Well as I was taking it off she pushed me towards the bed. I landed on my back and looked up to see mom lifting the nightgown off. She walked over to her night stand and opened a drawer. She pulled out a dildo box and opened it. She took out a bottle of sex lube and showed me the dildo saying “won’t be needing this now will we?”
Mom straddled me, she grabbed my cock and pressed it to my belly so that she could sandwich it between her pussy lips and my belly. She started a fucking motion with her hips while sliding her slit back and forth on my cock. I could see her pussy lips flowering open to wrap around my shaft. I looked up to see her tits hanging down and swaying back and forth to her actions with her huge nipples pointing down. Mom had opened the bottle of sex lube and squirted a splat into her hand. She then seemed to pout saying “oh dear that is too much” she smiled and said “I know” then started slathering her tits in sex lube making them shine. Now mom was looking directly at me while massaging sex lube into her tits and asking me if I thought she was taking it too far. Quite honestly, I was at a loss for words.
Now with both her massive breasts shining wet she leaned forward and started whispering “no? Not to far yet?” I was totally speechless. She whispered to me “I don’t need the lube down there, I’ve been wet since we started this game” Then she tilted her hips up and I felt her oil slicked hand grab my cock. She aimed me right for her open slit and impaled her self in one push spearing my cock to the hilt in her sopping wet pussy slit.
Now mom sat back up and began grinding her hips forward and back. I’d like to say I was a champion and fucked her till she got off, but she had me so turned on that I just started unloading inside of her. She must have felt my first spurt which would have flown over her head if it was on the outside. Her eyes popped wide and she pulled back pulling my cock out of her slippery wet hairy hole. Using her still lubed hand she began jerking me off with the next two shots of my load hitting the underside of her sagging breasts. She then pointed my dick more towards her belly and emptied my balls right there.
Afterwards she smiled and said “it looks like your little man here likes mommies games too doesn’t he?” On our second and third bouts I was able to get mom off before she let me just unload it all right up inside of her.
This was the start of a very, very good year for me.
